Questions to Ask in the Talking Stage (Without an Interview Vibe)

The best questions to ask in the talking stage aren't the deepest ones. They're the ones that show you something specific: what this person cares about, how they treat the people around them, how they'd actually be with you and whether your pace matches. Below are 16 questions sorted by what they reveal, roughly in the order you'd use them, each with what's worth noticing in the answer. One rule makes all of them work: answer your own question too. Otherwise even a great question turns into a job interview.

Quick definition, in case that's what you searched: the talking stage is the stretch after you've started texting or going on dates but before you've agreed to be exclusive or call it a relationship. Think "we're getting to know each other." How long it should last is its own question, and how long the talking stage should last gives a rough benchmark.

These are getting-to-know-you questions. The heavier ones about exclusivity, kids and money belong closer to making it official, and questions to ask before dating someone covers those.

The rule: trade, don't interrogate

Most talking-stage questions are fine. The delivery is where it goes sideways. Three habits fix most of it:

• Go first, or right after. "I'm a total Sunday-reset person. Laundry, groceries, long walk. What's your Sunday like?" is easier to answer than a bare "what do you do on weekends?"
• Follow up before you move on. If they say they just got into climbing, "Bouldering or ropes? Are you scared of heights?" beats jumping to "Cool, what music do you like?" Curiosity lives in the second question, which is what our lesson on curious questions practices.
• One question per text. Three in a row over text feels like a form.

If conversations keep feeling one-sided, conversation feels like an interview? covers the fix in detail. A simple order that keeps things balanced: talk about them, talk about you, then talk about the two of you. That's the backbone of our lesson her, me, us, and it works no matter who you're dating.

Questions that show what lights them up

These are light enough for texting or a first date.

1. "What's the last thing you stayed up way too late doing?" More fun than "what are your hobbies?" and more honest. Whatever makes someone lose track of time is usually something they really care about: a whole season of a show, a rabbit hole of camping-gear reviews, a 2 a.m. conversation with an old friend. If their face lights up, keep following it.

2. "What's something you spend money on that other people don't get?" Sneakers, coffee gear, concert tickets, a fantasy football league with real stakes. This isn't about money. It shows you what their enthusiasm looks like, and whether they can own being a little weird about something.

3. "What did you want to be when you were a kid? What happened?" Sounds like small talk, but you'll hear how they talk about change: laughing about it, or a little wistful. How someone describes a dream they let go of says something about how they handle disappointment.

4. "What's the last thing that made you laugh so hard you couldn't stop?" Checks whether your senses of humor line up. Notice what they find funny, too. If the best stories are always about someone else getting humiliated, that's information.

Questions that show how they treat people

5. "Who's the friend you've known the longest, and how have you stayed close?" How someone keeps a friendship going is a decent preview of how they keep a relationship going. Annual birthday dinners, a group chat that never dies, a standing call. Worth noticing: nobody they've stayed close to for long, and every friendship ending because the other person was the problem.

6. "What's the worst coworker situation you've dealt with? How'd it end?" This one's gold. You'll hear whether they deal with conflict directly, avoid it, or vent and move on. If they describe a coworker with real contempt, that's a preview of how they might talk about you during a fight.

7. "When's the last time you apologized to someone?" Save it for when you're a little more comfortable, keep the tone light, and share yours first. People who can name something they got wrong tend to be better at repairing after an argument. Blanking is normal. "I don't really mess up" is worth a second look.

8. Not a question, but watch: how they treat the server, the barista, the rideshare driver. The order comes out wrong, the wait runs long. That moment says more than any dating profile.

Questions that show how they'd be with you

9. "Are you a texter or a caller?" Sounds small. It's one of the most common sources of friction in the talking stage. Some people feel a day without texting means things are cooling. Others find ten texts a day exhausting. Ask early and save yourself a lot of decoding.

10. "When you get slammed, how do you usually let people know?" Some people send "crazy week, I'll be slow." Others disappear for three days and resurface like nothing happened. Knowing their habit means slow replies won't send you spiraling later. Share yours too.

11. "When you've had a terrible day, what helps: company, advice or being left alone?" Maybe the most useful question on this list. Some people want someone next to them. Some need to be alone first. Knowing ahead of time means you don't have to guess at the worst moment.

12. "What do you do when someone misunderstands you?" Lighter than "how do you fight?" but it shows you something similar: whether they explain right away, cool off and come back, or go quiet. The answer to notice: "I just stop talking to them until they figure it out." That's not cooling off. That's the silent treatment.

Questions that show whether your pace fits

13. "Do you warm up to people slowly or fast?" It asks about their pace without the weight of "so what are we?" If they're a slow warmer, three dates of slight stiffness makes more sense.

14. "How often do you like to see someone you're dating?" No right answer, but a big gap gets tiring fast. Better to find out now than later, when one of you feels neglected and the other feels crowded.

15. "Do you like surprises, or do you like knowing the plan?" Very practical. For a plan person, give a day, a place and a rough length when you ask them out. For a surprise person, leave a little room. It also tells you how comfortable they are with uncertainty.

16. "Do you like your friends to meet someone early, or wait until it's official?" Some people bring you to a friend's barbecue by week three. Others keep things private until there's a label. Both are normal, and knowing which one you're dealing with keeps you from reading "haven't met their friends yet" as being hidden.

Questions to hold off on (and why)

• Salary, savings, credit score. They matter eventually. In the talking stage they come across as an appraisal. Bring them up when you're actually discussing a future.
• Sexual history and the gory details of their last breakup. Exes can come up, but "what did your last relationship teach you?" is far easier to answer than "why did it end?" For how far to go, see talking about your ex on a date.
• "So, do you like me?" at 1 a.m. over text. You can absolutely ask. Just do it in person, at a relaxed moment, after saying where you stand. Our free lesson Not sure? Ask has wording that doesn't make it awkward.
• Trick questions designed to be "passed." Elaborate hypotheticals about who they'd save from a burning building. Nobody asks those to hear the answer. They're tests, and people can tell.

Want deeper material later on? The 36 questions are built for two people to answer in turns, not for one person to quiz the other. More on dates lives on our dating topic page.

FAQ

What do you talk about in the talking stage?

Mostly ordinary stuff: what happened today, what they're excited about, something funny you saw. The questions above help you go a level deeper, but the real move is following up on what they say and adding your own version.

Is it okay to ask about exes in the talking stage?

Yes, gently. "What did your last relationship teach you?" is easier to answer than "why did it end?" and doesn't feel like a deposition. If they don't want to get into it, move on.

Should I ask these over text or in person?

The first two groups work fine over text. The last two are better in person, where you can read their face and follow up. Heavy questions don't belong in 1 a.m. texts.

What if they never ask me anything back?

First check whether you're asking so much they don't have room. Share a bit more about yourself and leave an opening. If several dates in they still show no curiosity about you, that's an answer in itself.